1-Hydroxybenzotriazole → Benzyl carbamate

HRID 1247372Notes

Reaction equation

HRID 1247372 reaction equation
FC1C=C(OC2C=CC(OC)=CC=2)C=C(F)C=1C(OCC)C(O)=O.Cl.Cl.[CH2:27]([O:34][C:35](=[O:47])[NH:36]C(C1C=CC(CN)=CC=1)=N)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(N(CC)CC)C>[CH2:27]([O:34][C:35](=[O:47])[NH2:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21904916(RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acidHCID 141089245Carbamic acid, [[4-(aminomethyl)phenyl]iminomethyl]-, phenylmethyl ester, dihydrochloride

Product 1

HCID 12136Benzyl carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

(RS)-[2,6-Difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid (398 mg) was dissolved in DMF (15 ml). [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester dihydrochloride [Prepared according to Ch. Lila, Ph. Gloanec, L. Cadet, Y. Hervé, J. Fournier, F. Leborgne, T. J. Verbeuren, G. De Nanteuil, Synthetic Communications 1998, 28, 23, 4419–4429] (367 mg) and 1-hydroxybenzotriazole (254 mg) were added and the mixture was cooled to 0° C. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (254 mg) and triethylamine (1.38 ml) were added and it was stirred 1 h at 0° C. and 5.5 h at rt. The solvent was evaporated and the residue was taken up in H2O (40 ml) and CH2Cl2 (30 ml). The organic layer was separated, washed with brine and dried (MgSO4). The aqueous layers were extracted with two more portions CH2Cl2. After evaporation of the solvent CC(CH2Cl2 to CH2Cl2/MeOH 98:2) afforded 228 mg (32%) of (RS)-[4-(12-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-2-ethoxy-acetylamino)-methyl)-phenyl]-imino-methyl}-carbamic acid benzyl ester. White foam. MS 602.0 ([M−H]−).

Workup

  1. customThe solvent was evaporated
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. extractionThe aqueous layers were extracted with two more portions CH2Cl2
  6. customAfter evaporation of the solvent CC(CH2Cl2 to CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-1001c73e2e0c4bada976b2a54ce22f87
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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